


Jester Butts In

by bboiseux



Series: Critical Role Relationship Week 2018 [7]
Category: Critical Role (Web Series)
Genre: A little implied sexual confusion on the part of Yasha, Anal Fingering, CritRole RSWeek 2018, Double Penetration, F/F, F/M, Just fun and soft sex to take care of the team's sad barbarian, Long Live Feedback Comment Project, Multi, Oral Sex, Plot What Plot/Porn Without Plot, Rimming, Strap-Ons, Threesome, Two friends fucking, then three friends fucking
Language: English
Status: Completed
Published: 2018-06-23
Updated: 2018-06-23
Packaged: 2019-05-26 17:56:23
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,253
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15006248
Author URL: https://archiveofourown.org/users/bboiseux/pseuds/bboiseux
Summary: Sex is just an itch that Yasha sometimes needs to scratch.  Like when she's angry or frustrated.  And when she needs a helping hand, Molly has been there.  This time, however, Jester walks in and Yasha discovers that sex can be so much more than just an itch to scratch.  Jester, Yasha, and Molly have a threesome.For Relationship Week 2018Reading Time:abt 22 mins.





	1. Mollymauk

**Author's Note:**

> First, I make absolutely zero apologies for the pun. I find it hilarious.
> 
> Second, this is a spiritual sequel to [A Knock at the Door](https://archiveofourown.org/works/13713945). Together they make an informal series that's best called "Jester Interrupts Sex and Proceeds to Make that Sex Even Better."
> 
> Third, this is a bit of a speed run for anal. If you are actually doing this for the first time, please take your time and don't rush the experience.

The door smashed against the wall with a bang (and a light fall of plaster) and Yasha strode into the room.

Molly, who was reclining on the bed filing his nails, noted her arrive with a slight turn of his head and then went back to his work.  "Everything alright?"

She growled, "I'm tense."

"Anything you'd like to talk about?"

"No."  She prowled the room, eyeing Molly.  On her fifth pass, she grabbed the door and slammed it shut.  This time, some plaster fell from the ceiling.

Molly blew the dust from his nails and tucked the file away, swinging his body around and planting his feet on the ground.  As he stood up, he shrugged his coat off (revealing the seductive curves of his body, trimmed with illustrations) and tugged at his belt buckle.  "This?"

"Yeah." Yasha grappled with her bindings, dropping her sword to the floor, and pulling off her top (muscles rippled under a sea of pure white).  She growled deep in her throat.  "I need to work this out."

Molly kicked his pants off and stood waiting as Yasha approached, working his lavender cock to firm attention. "Do what you need.  I'm here for whatever."

Yasha stepped forward and shoved him back.  He fell, legs spread, and gripped the mattress above his head with both hands.  He knew enough to keep hands off when Yasha was like this.  Towering over him, Yasha popped the fastenings from her pants and tore them off.  She left the boots on.  Stepping onto the bed, she straddled Molly, one hand steadying on his bare chest, the other reaching under to pull his cock to her cunt.

Molly sighed into the feeling, as she ran the tip back and forth.  "You're a little dry.  You sure you don't want some foreplay?  My tongue is—"

"No."

Molly also knew enough to shut up.

Yasha played his cock against her cunt a few more times and then dropped down, all the way down, pushing him as deep inside as she could.  Molly groaned, Yasha's cunt rough and gritty as it slid down his shaft.  She readjusted for a moment, all business, and then she went to work.  Her hips bucked, both of her hands pressed intensely against Molly's chest, her back curved, her head down, black and white hair obscuring her face.  She ground into his hips, painfully hard, almost bone against bone, her legs clamping him in place as her ass and hips and abs and waist swiveled in tight circles.  She grunted in time to the movements, flicking his cock inside her in a steady rhythm.

Her hands clutched at his bare chest, her fingers kneading his skin, nails haphazardly digging in.  She angled her pelvis, so that her pubic hair scoured his groin.  Molly felt her go hot and slick.

Yasha pounded him into the bed.  Her hard body slamming him downward with each thrust of her hips.  The wooden bedframe jumped into the air and then cracked against the floor.  She grunted, all sweat and effort and focus.  Her arms tense and rigid.  Her skin glistening.  Her eyes closed.  Her face strained.  Molly's knuckles were white, clinging to the mattress.  Every jerk of Yasha’s body was concentrated, delicious violence.  With each pounding motion, Molly could feel his own pressure building.  One of Yasha’s hands worked up to his throat, then his face, and he fought off the urge to nip and suck at her fingers.

Molly didn’t know what he noticed first.  It might have been the light smack of the door falling open against the wall.  It might have been a tiny squeak escaping from blue tiefling lips.  Either way, he looked past the tremors of Yasha’s body and saw Jester frozen in the doorway.

She must have noticed him looking because she waved and said, “Oh, hi, Molly. Um . . . this looks pretty fun.”

Molly patted Yasha on the arm.

With a glare, she rumbled, “What.”  It came deep from her chest.  She didn’t stop.  Her grunts were turning to whimpers.

“I’m sorry, dear,” said Molly, “But we have a visitor.”  He gestured towards the door.

Yasha’s head jerked around and the force of the movement almost tossed her off the bed.  Molly’s cock fell out, burnished with her juices, and smacked against his pelvis.

“Je—Jester?”  The rage completely drained out of Yasha’s voice, her ashen skin suddenly glowing a slight shade of pink.  “Um, we were just—” She looked at Molly and the disheveled state of the bed and then down at her own glistening naked body.  When she spoke again, it was her usual deadpan, “Well, I just had to work off some steam, you know?  It’s—it’s a good way to work off some steam.”  She flushed even pinker.

Jester nodded enthusiastically.  “Oh, yes, that is definitely true.  I personally find it very invigorating.”  She didn’t show any signs of leaving.

Yasha stuttered out, ‘Um, so we’re . . . sort of . . . .”  She was suddenly acutely aware of how naked she was and just gave a general “all of this” gesture with one hand, indicating the fact that she was, yes, still naked, straddling Molly.

It took a few moments, but the situation seemed to sink into Jester’s mind.  “Oh!  You probably want to finish.  Have fun!”  She turned and started to close the door, but then hesitated and said, “You, um, you are a very attractive woman, Yasha, and, if you every want to, I would be happy to relieve any stress or tension that you have.  Okay?"  Jester couldn't help stealing a look at the dripping gray and pink of Yasha's cunt, where it peaked out below her firm round ass.

Yasha radiated a vibrant pink glow. "Oh, well, I like something hard to work with when I'm like this."  Yasha chuckled stiffly.  "So I guess if you've ever got a cock you want to pound me with, uh, well, look me up!"  She punctuated the whole thing with an awkward smile.

Molly was barely restraining his laughter.  Yasha smacked him.  "Shut up," she hissed under her breath.

When she turned back Jester had her bag on the floor and was pulling out a blue object.  To her horror, Yasha realized (as it wobbled wildly back and forth) that it was a two-foot-long, double headed dildo.  Jester gave it a quick look over and draped it over her shoulder, digging back into the pack.  "That’s probably too big, huh?  How about--" Here she pulled a small black dildo out of the bag, attached to some straps.  "--this!"  She held it up triumphantly and the big blue dong bounced off the floor.  Jester quickly grabbed it and shoved it back into the bag.  When her hand came out again, it was holding a brown bottle.  "It is very important to have your strap-on and lube handy at all times."  She shot Molly and Yasha a broad smile.

There was a long pause and then Molly flung his head back in a laugh, clapping his hands in dramatic applause.  "She's got your number, Yasha.  Would you like the room, you two?"

Jester pouted.  "Oh, Molly, you do not want to play too?"

"Well, I think all of this is up to our good friend Yasha.  What do you think?"  He shot Yasha, still leaning over him, a good-natured smile.

"Ah, well, um," Yasha began with a splutter, "I mean, that's really flattering and all, but--" She looked back and forth between Molly and Jester (all eager eyes, strap-on dangling from one hand) and then sighed.  "Look, I expect this to be the most satisfying fuck I've ever had, okay?"


	2. Jester

A minute later, before Yasha had even thought to climb off Molly, Jester was completely naked and was tightening the last strap.  She gave a little thrust and waggle with her hips.  The black cock stayed firmly at attention. "Yep, I think that's perfect."  She looked over the beautiful tableau in front of her: Molly's leg's spread wide, his cock lolling on his pelvis, and, right above, Yasha's powerful haunch framing the pink explosion between her legs.

Yasha was peering, flustered, over her shoulder, musclebound arms still locked on Molly's chest.

"Yasha?" asked Jester, "May I lick your pussy?"  She thought a moment and then added, "And your ass?  And maybe just touch you all over?"

If Yasha had glowed pink before, there was now a sharp shade of scarlet spreading across her face.  "Well, I—whew—that's quite an idea."  She stumbled over the words.  "I—I think I'd like that.  How about I tell you if I want you to stop."

Jester gave an excited clap and kneeled between Molly's legs, giving his thighs a playful squeeze on the way down.  “Molly, are you okay with this?”

“Whatever works for Yasha.  I’m happy to go along for the ride.”  Molly was practically lounging, Yasha poised above him, Jester between his legs.

Jester grinned. “Yasha, I think you will like this."  Resting her hands on Yasha's buttocks, Jester gave a hearty lick along her cunt.  Yasha gasped.  Jester licked again and again--long, lapping strokes caressing the gray lips, teasing the pink flesh.  The savory taste dripped across her mouth and Jester hummed with delight.  "You taste delicious."

Yasha could only stutter out, "Je-Jester" before Jester buried her face in Yasha's cunt again and she was reduced to a breathy “oh.”

Beneath her, Molly smiled wickedly, hands resting casually behind his head, and said, "Keep up the good work, Jester.  You must be doing something right."

"Fu-fu-fuck you, Molly," came Yasha's response.  She was gripping Molly's shoulders, pushing back into Jester's face.  Her eyes were closed, head up towards the ceiling, mouth slightly open.  Her dark hair cascaded down her back.

Below, Jester gobbled at Yasha's cunt, pushing deep with broad, sweeping motions of her tongue, stopping to suck and tease and pull as she went.  She liked the way Yasha's muscles shuddered every time she grazed her clit.  She especially liked how the muscles in Yasha's ass seemed to vibrate under her hands, a veritable earthquake.  And that gave Jester a fun idea.

Face glistening with Yasha's juices, Jester sloppily ran her tongue from Yasha's clit all the way to her ass.  She squeezed Yasha's cheeks apart and teased at her asshole, attentively stroking with the tip of her tongue.

"Oh, okay," gasped Yasha.

Jester pulled away, wiping her mouth and chin.  "Do you like it?"

Between pants, Yasha said, "It feels different and weird.  I--I don't know.  Keep doing it."

Jester dove back to Yasha’s ass, playfully licking down her crack, teasing for a moment, then kissing and sucking on Yasha’s buttocks before sloppily returning to her asshole, slurping hungrily with her whole tongue.  Yasha leaned back further, pushing more of her ass towards Jester.  Jester giggled around her tongue and pulled back a little.  “So you do like that!”

Yasha went to answer, but it was lost to a groan as Jester leaned in again, gripping Yasha’s hips, trapping her in place.  She lavished adoring attention on Yasha’s ass.

Minutes later, Yasha was whimpering into Molly’s chest, her hands clutching at his horns, her body collapsed against his, as Jester gave a last lingering lick.  Jester fell back, biting her lip, and tentatively pressed a finger to Yasha’s asshole.  Yasha quivered at the touch and Jester smiled, a hand playing across her strap-on.

“Yasha, have you ever had two dicks at once?”

It was a minute before Yasha could answer, her breaths heavy, her body heaving.  “I—I’ve never thought about it before.  What—what would it involve?”

Jester pulled herself up on Molly’s legs and wrapped her arms around Yasha’s waist.  The black cock pressed flat against Yasha’s ass.  “Well—” She ran one hand down the front of Yasha and played lightly with her clit (Yasha gasped and bit down on her lip).  “Molly would go here and then—” She thrust a little with her hips, pushing the strap-on lightly against Yasha.  “—I would go here.”

Beneath her, Molly spoke up.  “It would be a particularly interesting sensation.  I’ve never experienced it that way, but there’s something quite satisfying about being completely filled up that I highly recommend.”

“It can be really good, Yasha.  I think you’ll like it,” said Jester, “And if you don’t, you say so and we stop!”

Yasha worried her lip and then pushed back up onto all fours.  She could feel Jester’s warm body wrapped around her ass and back.  “How much will you touch me?”

Jester let go completely.  “Only as much as you want.  Do you want me to touch you?”

“Yes.  Yes, I really do.”

Jester ran a finger down the valley of Yasha’s back and watched her squirm under the light touch.  She grinned hungrily at Yasha.  “How much?”

“As much as you want.”

Molly was grinning too, but he looked at Yasha softly.  “Finally figured it out, eh?”

“Maybe,” she whispered.

Behind her, Jester had opened the bottle of lube and was warming the slickness between her hands and rubbing it over the strap-on.  “Would you like me to start?”

“Ah, um, okay.  What are you going to do?”

Jester looked down and shook her head.  “Well, I guess the first thing I’m going to do is get Molly hard again.”  She kneeled down. “What’s the matter, Molly, aren’t two smoking hot ladies enough for you?”

Molly laughed, arms still reclined casually behind his head.  “Guess I’m just hard to please.  Throw in a few more people of various genders and I’ll see what I can do.”

Jester blew a raspberry and grabbed his cock, stroking the shaft gently.  “Maybe you should try focusing on someone else’s pleasure for once.”  She kissed Yasha’s thigh and then sloppily licked the head of Molly’s cock.

Molly sighed.  “You’re going to make that a tad difficult.”

Jester gave a hearty suck (coming off with a loud pop) causing Molly to let out a disgruntled “Yow!”

“Behave, Molly.”

She lowered her head again, slurping heartily at Molly, letting her tongue and lips roll down the shaft.  When she pulled off, he was fully at attention, and she distractedly kept working him with one hand, while she regarded Yasha’s cunt.  She reached up and massaged her with her lube slick hand, feeling the heat radiating through the coarse pubic hair.

Jester pushed herself up, lavishing kisses on Yasha’s buttocks as she rose.  “Yasha, I’m going to get you started on Molly and then I’m going to open up your ass with my fingers.”  One hand still on Molly’s cock, she toyed with Yasha’s asshole.  “When you’re ready, I’ll fill you up with my little cock.”  Jester felt hot just thinking about it.  “Are you ready for me to start?”


	3. Yasha

Molly was below her, filling her vision, but her mind narrowed to the heat of Jester’s hands on her ass and the ring of Jester’s voice in her ears.  Something had changed the moment Jester came in the room and Yasha didn’t know what to do.  Every touch (the grip of a hand, the caress of a tongue, the brush of her hair) stoked a fire in her belly that she didn’t know could burn like this.  It has searing.  It craved more fuel.  And that fuel was Jester.

Yasha took a long breath.  “Yeah, I’m ready.  Just, you know, warn me if you’re going to do anything different.”

The bed creaked and Jester was kneeling next to Molly.  This was the first time Yasha had gotten a good look at Jester since they had started.  And she was gorgeous, all soft curves, so different from the hardness Yasha was used to.

Jester brought a hand to Yasha’s face (wet with lube, but Yasha didn’t care) and pulled her into a soft kiss, Jester’s tongue sweeping along Yasha’s lips as she pulled away.  “I want this to be really good for you, so tell me the moment you want to stop.”  She looked over at Molly, scowling. “And try and keep your dick hard for a little bit, okay?”

Molly simply shrugged.  His grin fixed on his face.  Yasha loved Molly, but sometimes she hated the way he seemed to laugh at the world.

Jester climbed back down, her fingers brushing across Yasha’s side.  She shivered at the touch and almost laughed.  “That tickles.”

Jester’s arms wrapped around Yasha’s waist again, hugging their bodies close.  “That’s good!  Sex should be lots of fun.  If you can laugh during sex you know you’re having a good time!”  Then her arms (so cushy, but Yasha could feel the powerful muscles working underneath) pulled Yasha down.  “Let’s get Molly in you and then we’ll see what I can do.”  Wet lips worked their way up Yasha’s back as she kneeled back.

Beneath her, Jester gripped Molly’s cock and played it against Yasha’s cunt.  Slick with her juices, it slide quickly inside and Yasha let out a surprised gasp.  Jester held her in place, shifting Yasha back slightly.  The base of Molly’s cock pressed hard against her clit.  She instinctively swiveled her hips to grind against it, reveling in the sharp pleasure that radiated up into her belly.

She could hear the grin in Jester’s face.  “That’s a much better position for you, I think.  Now I’m going to give some more love to your tasty asshole!”

Jester’s hands massaged Yasha’s ass apart again and then the soft slick slide of her tongue was back all wet caress and warm breath.  Yasha pushed back into Jester’s waiting mouth, yearning for the intense feeling of Jester’s face crushed into her ass, but the push ground her clit against Molly’s cock again and her head went light.  She jerked forward, grasping at Molly’s chest to keep her balance.

Jester sat back and reached for the bottle of lube.  “Time to open up that ass!” she announced.

There was the sound of lube being warmed (all squishy suck) and then Jester’s finger was on Yasha’s asshole.  It was a point of heat, pressing in, a bizarre feeling where her body both wanted to open to Jester and tighten up, closing her out.  Jester pushed in, massaging in little circles as she went, warming and teasing until the tip of her finger penetrated through.  Yasha quivered at the feeling of Jester moving that little piece of herself in and out of her.  Pushing in, breaking that barrier, then pulling out, extending her just a bit.  It stung, but it also felt right.  Inside her, Molly twitched.  Yasha groaned behind closed lips.

“Oh, Yasha, you’re really good at this!”  Jester’s voice bounced with excitement.  “Are you ready for two fingers?”

Lips and eyes sealed shut, all senses focused on what Jester and Molly were doing to her, Yasha nodded her head quickly.

Jester pulled her finger away and Yasha sighed at the loss, but then she was back just as quickly, two fingers massaging, warming.  And they were inside.  Yasha couldn’t believe how big just two fingers felt, sliding in and out. Jester flexed them apart and Yasha had to catch herself as all her breath erupted in one gasp.  Instinctually, she pushed back onto Jester’s hand and Jester held firm, letting Yasha’s asshole swallow her fingers.

“Wow, Yasha, all the way to the knuckles already!” said Jester.  She squirmed the fingers in and out in a steady thrusting motion.  “That feel right?”

Yasha meant to say “yes,” but it came out a low rumbling “fuck!” as Jester pushed all the way in with a twist and then pulled completely out.  Yasha collapsed on Molly’s chest, whimpering.

Jester kept working the fingers in and out, applying more lube just when the sting seemed to be growing, massaging Yasha’s asshole with her free hand and slowly widening the fingers as she went.  It must have been minutes, but Yasha wasn’t sure.  She just knew that it was unlike anything she had ever felt before.  She was stretched wide to Jester.  She felt vulnerable.  And she didn’t care.  She wanted Jester to spread her wide and fill the aching gap the fingers created.

Head lolling down Molly’s shoulder, mouth open, gasping for breath, Yasha said, “More.  Please.  Jester.  I want you.”  It was halting, between staggered breath, but Jester heard her.  Slowly, Jester pulled the fingers out, until Yasha felt their absence.  Molly was motionless inside her and she took a moment to breath.

Behind her, Jester massaged lube into the strap-on and positioned herself behind Yasha.  “Okay, Yasha, I’m going to fuck you now.  Do you want that?”

Yasha burned for it.  “Yes.  Now.”  She didn’t want any ambiguity.  She wanted Jester inside her immediately.

After everything, Yasha was shocked how tight she was.  Jester had to work the cock into Yasha’s ass a little at a time, but when it finally pushed through, Yasha whined.  She had seen it.  It was just a little thing.  But it felt enormous.  Far bigger than Jester’s fingers.  At first, Jester worked a little of the cock in and out at a time and Yasha felt stretched to her limit, each little thrust brought a gasp to her lips.  When Yasha seemed comfortable with that, Jester started increasing the strokes, increasing the inches she was giving Yasha, until she was driving the whole cock into Yasha’s ass and then pulling it right to the tip.

Yasha let out a sound between a groan and a wild yowl as Jester pushed deep and she gripped the mattress on either side of Molly’s head, her arms pinning Molly’s in place.  Her mind was fixed only on the idea that she needed Jester to pound her hard, she needed more, she needed faster.

“More,” Yasha moaned between gasps.

Jester gripped her cheeks tight, spreading them, massaging them firmly, and holding her in place against Molly.  The world became the steady smack of Jester’s hips against her buttocks, the juicy suck of Jester’s cock moving in and out of her ass, the sweet aching sting and sharp tingling pleasure of Jester inside her overwhelming every other sense.

She heard Jester say “Molly, put your butt into it. Don’t let Yasha down” and Molly started moving.  Squeezed against him, held tightly in place by Jester, every thrust was like Molly was hitting a button that made Yasha’s vision go white, a squealing sharp sensation that jolted through her spine.  Behind her, Jester was deep in her ass now, her hips grinding against Yasha’s buttocks, each tight thrust stretching her open, making her moan wider.  She could feel both of them sliding in and out of her, both filling her tightness.  She tried to lift her body, but the next thrust from Jester sent her right back down and she scrambled to hold on to the mattress again.

There was no build, not like usual.  Normally, it was a carefully angling to get just the right spot, just the right rhythm to make her body give that delicious explosion of pleasure.  Not this time.  One minute, she was groaning into the ecstatic feeling and the next moment she lost complete control.  Her thighs rippled and jerked, locking around Molly (there was a twitch and a warm smack as he came, moaning, eyes rolling up in his head).  Her ass bucked wildly, pressing against Jester, who leaned in, pinning her in place, angling her cock even deeper.  Yasha’s abs tensed, sending waves through the rest of her body.  And she squealed, genuinely squealed, a heady pitch that she didn’t even know she could make.  It was like her whole body had broken to pieces and then slammed back together.

She had already collapsed, so she lay in a sweaty heap, the aftershocks coursing through her body.  Molly was below her, his chest heaving for air.  Jester was on top of her, thrusting lightly and erratically kissing Yasha’s drenched skin.  She didn’t know why, but here, completely naked and vulnerable, she felt protected by these two bodies.

Jester pulled out and sprawled sideways on the bed, matching Molly’s position, and Yasha rolled to the side, putting her self between the two tieflings.  Both of them were grinning.  Yasha wore more of a stunned expression.

“Well,” said Jester, “What did you think?”

Yasha took a deep breath.  “I think that was . . . very good.”  She nodded firmly.  “Yes, very good.”

Jester stretched out and yawned.  “At this point I like to cuddle,” she said, “Do you like to cuddle, Yasha?”

“Ah, well, I—that is, I don’t.  Well, I don’t know.”  Yasha ran her eyes over Jester’s naked body, lingering over the large blue nipples that puffed up like mountains, the tummy roll that arched into . . . well, a little black cock, currently.

Jester followed her eyes and giggled.  “First rule of cuddling is hard dicks get in the way.”  She undid a strap and wiggled it the rest of the way off.

Molly stood up.  “Well, that seems like my sign to give you two some peace.”  He grabbed a robe off the footboard and threw it on.  “You two take all the time you need.  The room is yours.”  He leaned over and kissed Yasha on the forehead. “Please enjoy,” he whispered to her.  Then he was gone, closing the door after him.

When Jester looked back at Yasha, she noticed that her eyes were staring at her breasts.  “You can play with them, if you’d like.  That can be fun too.  Oh, Yasha, there are so many things I can teach you!”

**Author's Note:**

> I am also [bboiseux on tumblr](https://bboiseux.tumblr.com/).
> 
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